Mayr's Database Of Reactivity Parameters
AK Prof. Mayr

O-Nucleophiles

For reactivities of structurally related compounds go to: Nucleophiles
Found 88 Molecules.
Molecule Solvent Reactivity Parameters Classification Reference (sort by title or year)
image of molecule

(Z)-2-phenyl-1-(1,3,4-triphenyl-4H-1,2,4-triazol-1-ium-5-yl)prop-1-en-1-olate (in THF)
THFN  Parameter: 16.73
sN Parameter: 0.63
**Angew. Chem. Int. Ed. 2013, 52, 11163-11167
DOI: 10.1002/ange.201303524
image of molecule

1% water/99% HFIP (w/w)
water-HFIP mixN  Parameter: -1.93
sN Parameter: 1.09
***J. Phys. Org. Chem. 2013, 26, 59-63
DOI: 10.1002/poc.3064
image of molecule

10% ethanol/90% MeCN (v/v)
EtOH-MeCN mixN  Parameter: 5.19
sN Parameter: 0.96
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
image of molecule

10% methanol/90% MeCN (v/v)
MeOH-MeCN mixN  Parameter: 5.55
sN Parameter: 0.97
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
image of molecule

10% water/90% acetone (v/v)
water-acetone mixN  Parameter: 5.70
sN Parameter: 0.85
***Angew. Chem. Int. Ed. 2004, 43, 2302-2305
DOI: 10.1002/anie.200353468
image of molecule

10% water/90% HFIP (w/w)
water-HFIP mixN  Parameter: 0.96
sN Parameter: 0.93
***J. Phys. Org. Chem. 2013, 26, 59-63
DOI: 10.1002/poc.3064
image of molecule

10% water/90% MeCN (v/v)
water-MeCN mixN  Parameter: 4.56
sN Parameter: 0.94
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
image of molecule

10% water/90%EtOH (v/v)
water-EtOH mixN  Parameter: 7.03
sN Parameter: 0.86
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
image of molecule

10% water/90%TFE (v/v)
water-TFE mixN  Parameter: 2.93
sN Parameter: 0.88
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
image of molecule

2% water/98% HFIP (w/w)
water-HFIP mixN  Parameter: -1.62
sN Parameter: 1.10
***J. Phys. Org. Chem. 2013, 26, 59-63
DOI: 10.1002/poc.3064
image of molecule

2,2,2-trifluoroethanolate (in water)
waterN  Parameter: 12.66
sN Parameter: 0.59
***J. Am. Chem. Soc. 2003, 125, 286-295
DOI: 10.1021/ja021010y
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2-phenylperoxyacetate (in H2O)
waterN  Parameter: 15.63
sN Parameter: 0.56
***Angew. Chem. Int. Ed. 2017, 56, 13279-13282
DOI: 10.1002/anie.201707086
image of molecule

20% ethanol/80% MeCN (v/v)
EtOH-MeCN mixN  Parameter: 5.77
sN Parameter: 0.92
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
image of molecule

20% methanol/80% MeCN (v/v)
MeOH-MeCN mixN  Parameter: 6.04
sN Parameter: 0.94
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
image of molecule

20% water/80% acetone (v/v)
water-acetone mixN  Parameter: 5.77
sN Parameter: 0.87
***Angew. Chem. Int. Ed. 2004, 43, 2302-2305
DOI: 10.1002/anie.200353468
image of molecule

20% water/80% MeCN (v/v)
water-MeCN mixN  Parameter: 5.02
sN Parameter: 0.89
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
image of molecule

20% water/80%EtOH (v/v)
water-EtOH mixN  Parameter: 6.68
sN Parameter: 0.85
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
image of molecule

20% water/80%TFE (v/v)
water-TFE mixN  Parameter: 3.20
sN Parameter: 0.88
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
image of molecule

3% water/97% HFIP (w/w)
water-HFIP mixN  Parameter: -1.19
sN Parameter: 1.08
***J. Phys. Org. Chem. 2013, 26, 59-63
DOI: 10.1002/poc.3064
image of molecule

3,5-dichloroperoxybenzoate (in H2O)
waterN  Parameter: 17.93
sN Parameter: 0.50
***Angew. Chem. Int. Ed. 2017, 56, 13279-13282
DOI: 10.1002/anie.201707086
image of molecule

3,5-dinitrobenzoate (in acetone)
acetoneN  Parameter: 18.80
sN Parameter: 0.62
**J. Am. Chem. Soc. 2008, 130, 3012-3022
DOI: 10.1021/ja0765464
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3,5-dinitrobenzoate (in MeCN)
MeCNN  Parameter: 14.90
sN Parameter: 0.71
**J. Am. Chem. Soc. 2008, 130, 3012-3022
DOI: 10.1021/ja0765464
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3-chloro-4-methoxyperoxybenzoate (in H2O)
waterN  Parameter: 18.56
sN Parameter: 0.48
***Angew. Chem. Int. Ed. 2017, 56, 13279-13282
DOI: 10.1002/anie.201707086
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3-chloroperoxybenzoate (in H2O)
waterN  Parameter: 18.19
sN Parameter: 0.47
***Angew. Chem. Int. Ed. 2017, 56, 13279-13282
DOI: 10.1002/anie.201707086
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30% water/70% HFIP (w/w)
water-HFIP mixN  Parameter: 1.65
sN Parameter: 0.96
***J. Phys. Org. Chem. 2013, 26, 59-63
DOI: 10.1002/poc.3064
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33% ethanol/67% MeCN (v/v)
EtOH-MeCN mixN  Parameter: 6.06
sN Parameter: 0.90
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
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33% methanol/67% MeCN (v/v)
MeOH-MeCN mixN  Parameter: 6.38
sN Parameter: 0.92
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
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33% water/67% MeCN (v/v)
water-MeCN mixN  Parameter: 5.02
sN Parameter: 0.90
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
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4-fluoroperoxybenzoate (in H2O)
waterN  Parameter: 17.99
sN Parameter: 0.47
***Angew. Chem. Int. Ed. 2017, 56, 13279-13282
DOI: 10.1002/anie.201707086
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4-methoxyperoxybenzoate (in H2O)
waterN  Parameter: 17.84
sN Parameter: 0.46
***Angew. Chem. Int. Ed. 2017, 56, 13279-13282
DOI: 10.1002/anie.201707086
image of molecule

4-nitroperoxybenzoate (in H2O)
waterN  Parameter: 17.43
sN Parameter: 0.50
***Angew. Chem. Int. Ed. 2017, 56, 13279-13282
DOI: 10.1002/anie.201707086
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40% water/60%EtOH (v/v)
water-EtOH mixN  Parameter: 6.28
sN Parameter: 0.87
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
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40% water/60%TFE (v/v)
water-TFE mixN  Parameter: 3.42
sN Parameter: 0.90
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
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5% water/95% HFIP (w/w)
water-HFIP mixN  Parameter: -0.10
sN Parameter: 0.97
***J. Phys. Org. Chem. 2013, 26, 59-63
DOI: 10.1002/poc.3064
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50% ethanol/50% MeCN (v/v)
EtOH-MeCN mixN  Parameter: 6.37
sN Parameter: 0.90
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
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50% methanol/50% MeCN (v/v)
MeOH-MeCN mixN  Parameter: 6.67
sN Parameter: 0.90
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
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50% water/50% HFIP (w/w)
water-HFIP mixN  Parameter: 1.50
sN Parameter: 1.03
***J. Phys. Org. Chem. 2013, 26, 59-63
DOI: 10.1002/poc.3064
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50% water/50% MeCN (v/v)
water-MeCN mixN  Parameter: 5.05
sN Parameter: 0.89
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
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50% water/50%EtOH (v/v)
water-EtOH mixN  Parameter: 5.96
sN Parameter: 0.89
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
image of molecule

50% water/50%TFE (v/v)
water-TFE mixN  Parameter: 3.57
sN Parameter: 0.89
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
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60% water/40%EtOH (v/v)
water-EtOH mixN  Parameter: 5.81
sN Parameter: 0.90
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
image of molecule

60% water/40%TFE (v/v)
water-TFE mixN  Parameter: 3.77
sN Parameter: 0.88
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
image of molecule

67% ethanol/33% MeCN (v/v)
EtOH-MeCN mixN  Parameter: 6.74
sN Parameter: 0.89
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
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67% methanol/33% MeCN (v/v)
MeOH-MeCN mixN  Parameter: 7.01
sN Parameter: 0.91
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
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67% water/33% MeCN (v/v)
water-MeCN mixN  Parameter: 5.05
sN Parameter: 0.90
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
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7% water/93% HFIP (w/w)
water-HFIP mixN  Parameter: 0.34
sN Parameter: 0.96
***J. Phys. Org. Chem. 2013, 26, 59-63
DOI: 10.1002/poc.3064
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80% ethanol/20% MeCN (v/v)
EtOH-MeCN mixN  Parameter: 6.94
sN Parameter: 0.90
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
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80% methanol/20% MeCN (v/v)
MeOH-MeCN mixN  Parameter: 7.20
sN Parameter: 0.89
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
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80% water/20% MeCN (v/v)
water-MeCN mixN  Parameter: 5.04
sN Parameter: 0.89
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
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80% water/20%EtOH (v/v)
water-EtOH mixN  Parameter: 5.54
sN Parameter: 0.94
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
image of molecule

80% water/20%TFE (v/v)
water-TFE mixN  Parameter: 4.78
sN Parameter: 0.83
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
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90% water/10%EtOH (v/v)
water-EtOH mixN  Parameter: 5.38
sN Parameter: 0.91
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
image of molecule

90% water/10%TFE (v/v)
water-TFE mixN  Parameter: 5.04
sN Parameter: 0.90
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
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91% ethanol/9% MeCN (v/v)
EtOH-MeCN mixN  Parameter: 7.10
sN Parameter: 0.90
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
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91% methanol/9% MeCN (v/v)
MeOH-MeCN mixN  Parameter: 7.45
sN Parameter: 0.87
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
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91% n-propanol/9% MeCN (v/v)
nPrOH-MeCN mixN  Parameter: 7.05
sN Parameter: 0.80
***Can. J. Chem. 2005, 83, 1554-1560
DOI: 10.1139%2Fv05-170
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91% propan-2-ol/9% MeCN (v/v)
iPrOH-MeCN mixN  Parameter: 6.49
sN Parameter: 0.96
***Can. J. Chem. 2005, 83, 1554-1560
DOI: 10.1139%2Fv05-170
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91% water/9% MeCN (v/v)
water-MeCN mixN  Parameter: 5.16
sN Parameter: 0.91
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
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acetate (in 80A20W)
aq acetoneN  Parameter: 12.50
sN Parameter: 0.60
**J. Am. Chem. Soc. 2008, 130, 3012-3022
DOI: 10.1021/ja0765464
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acetate (in 90A10W)
aq acetoneN  Parameter: 12.71
sN Parameter: 0.68
***J. Am. Chem. Soc. 2008, 130, 3012-3022
DOI: 10.1021/ja0765464
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acetate (in MeCN)
MeCNN  Parameter: 16.90
sN Parameter: 0.75
***J. Am. Chem. Soc. 2008, 130, 3012-3022
DOI: 10.1021/ja0765464
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acetonitrile (in MeCN)
MeCNN  Parameter: 2.23
sN Parameter: 0.84
***J. Am. Chem. Soc. 2012, 134, 13902-13911
DOI: 10.1021/ja306522b
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benzoate (in 90AN10W)
aq MeCNN  Parameter: 11.30
sN Parameter: 0.72
**J. Am. Chem. Soc. 2008, 130, 3012-3022
DOI: 10.1021/ja0765464
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benzoate (in MeCN)
MeCNN  Parameter: 16.82
sN Parameter: 0.70
***J. Am. Chem. Soc. 2008, 130, 3012-3022
DOI: 10.1021/ja0765464
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cumene peroxy anion (in H2O)
waterN  Parameter: 13.92
sN Parameter: 0.61
***Angew. Chem. Int. Ed. 2017, 56, 13279-13282
DOI: 10.1002/anie.201707086
image of molecule

DMSO (O attack)
DMSON  Parameter: 11.30
sN Parameter: 0.74
***J. Am. Chem. Soc. 2009, 131, 11392-11401
DOI: 10.1021/ja903207b
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ethanol
EtOHN  Parameter: 7.44
sN Parameter: 0.90
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
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ethanolate (in 91E9AN)
EtOH-MeCN mixN  Parameter: 16.08
sN Parameter: 0.62
***Can. J. Chem. 2005, 83, 1554-1560
DOI: 10.1139%2Fv05-170
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ethanolate (in ethanol)
EtOHN  Parameter: 15.78
sN Parameter: 0.65
***Can. J. Chem. 2005, 83, 1554-1560
DOI: 10.1139%2Fv05-170
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H2O (in water)
waterN  Parameter: 5.20
sN Parameter: 0.89
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
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HOO- (in water)
waterN  Parameter: 15.40
sN Parameter: 0.55
***J. Am. Chem. Soc. 2003, 125, 286-295
DOI: 10.1021/ja021010y
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isopropanolate (in 91iPr9AN)
iPrOH-MeCN mixN  Parameter: 17.71
sN Parameter: 0.58
***Can. J. Chem. 2005, 83, 1554-1560
DOI: 10.1139%2Fv05-170
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isopropanolate (in propan-2-ol)
iPrOHN  Parameter: 17.03
sN Parameter: 0.63
***Can. J. Chem. 2005, 83, 1554-1560
DOI: 10.1139%2Fv05-170
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magnesium 2-carboperoxybenzoate (in H2O)
waterN  Parameter: 18.43
sN Parameter: 0.46
***Angew. Chem. Int. Ed. 2017, 56, 13279-13282
DOI: 10.1002/anie.201707086
image of molecule

methanol
MeOHN  Parameter: 7.54
sN Parameter: 0.92
***J. Am. Chem. Soc. 2004, 126, 5174-5181
DOI: 10.1021/ja031828z
image of molecule

methanolate (in 91M9AN)
MeOH-MeCN mixN  Parameter: 14.51
sN Parameter: 0.68
***Can. J. Chem. 2005, 83, 1554-1560
DOI: 10.1139%2Fv05-170
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methanolate (in methanol)
MeOHN  Parameter: 15.78
sN Parameter: 0.56
***Can. J. Chem. 2005, 83, 1554-1560
DOI: 10.1139%2Fv05-170
image of molecule

methyl carbonate (in MeCN)
MeCNN  Parameter: 16.03
sN Parameter: 0.64
***Eur. J. Org. Chem. 2010, , 4205-4210
DOI: 10.1002/ejoc.201000414
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n-propanolate (in 91nPr9AN)
nPrOH-MeCN mixN  Parameter: 16.73
sN Parameter: 0.63
***Can. J. Chem. 2005, 83, 1554-1560
DOI: 10.1139%2Fv05-170
image of molecule

n-propanolate (in propan-1-ol)
nPrOHN  Parameter: 16.03
sN Parameter: 0.70
***Can. J. Chem. 2005, 83, 1554-1560
DOI: 10.1139%2Fv05-170
image of molecule

OH- (in 50/50 water/MeCN)
water-MeCN mixN  Parameter: 10.19
sN Parameter: 0.62
***J. Am. Chem. Soc. 2003, 125, 286-295
DOI: 10.1021/ja021010y
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OH- (in water)
waterN  Parameter: 10.47
sN Parameter: 0.61
***J. Am. Chem. Soc. 2003, 125, 286-295
DOI: 10.1021/ja021010y
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p-nitrobenzoate (in acetone)
acetoneN  Parameter: 18.74
sN Parameter: 0.68
***J. Am. Chem. Soc. 2008, 130, 3012-3022
DOI: 10.1021/ja0765464
image of molecule

p-nitrobenzoate (in MeCN)
MeCNN  Parameter: 15.30
sN Parameter: 0.76
***J. Am. Chem. Soc. 2008, 130, 3012-3022
DOI: 10.1021/ja0765464
image of molecule

peroxybenzoate (in H2O)
waterN  Parameter: 18.57
sN Parameter: 0.43
***Angew. Chem. Int. Ed. 2017, 56, 13279-13282
DOI: 10.1002/anie.201707086
image of molecule

phthalimidoperoxyhexanoate (in H2O)
waterN  Parameter: 16.02
sN Parameter: 0.54
***Angew. Chem. Int. Ed. 2017, 56, 13279-13282
DOI: 10.1002/anie.201707086
image of molecule

t-butylperoxy anion (in H2O)
waterN  Parameter: 14.29
sN Parameter: 0.51
***Angew. Chem. Int. Ed. 2017, 56, 13279-13282
DOI: 10.1002/anie.201707086
image of molecule

trifluoroethanol
TFEN  Parameter: 1.11
sN Parameter: 0.96
***J. Am. Chem. Soc. 2012, 134, 13902-13911
DOI: 10.1021/ja306522b